


Choices

by randers1



Category: Chicago PD (TV)
Genre: F/M, Upstead
Language: English
Status: Completed
Published: 2020-07-24
Updated: 2020-08-05
Packaged: 2021-03-05 02:14:33
Rating: Not Rated
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 4
Words: 8,654
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/25496668
Author URL: https://archiveofourown.org/users/randers1/pseuds/randers1
Summary: Hailey is tired of waiting while Will tries to talk some sense in to Jay.
Relationships: Jay Halstead & Hailey Upton, Jay Halstead/Hailey Upton
Comments: 40
Kudos: 141





	1. chapter 1

**Author's Note:**

> None of these belong to me.
> 
> Hoping the story is follow-alongable (yeah that's not a word, I know)--kind of jumps around a bit.

“Hey-” He stopped short, quickly looking from left to right. A flash of a ponytail caught his eye as it turned a corner, and he charged forward, following it. “HEY!”

Hailey stopped just short of her locker, her jacket in hand, as Jay walked in, heavy footed and looking upset.

“Hailey?!” Jay huffed. “Hailey." He looked around the room and behind him in the hallway, confident no one else was nearby, and closed the door behind him. “What the hell was that?!”

Hailey put her hands up in a show of soft self-defense, completely unsure what had Jay so angry. “Wha--, what was what?” It was her instinct to be defensive but she fought to keep her tone pliant. It was difficult but until she knew what was going on she’d play it safe.

“You—we were—I don’t--“ He sputtered and ran a hand through his hair, stopping only to keep the hand at the back of his neck.

She put her coat down on the bench and took a step toward him, saying his name gently but firmly. “Jay.” One emphatic look was all she gave before speaking again, her hair swinging lightly as she spoke. “You’re gonna have to help me out here. I have no idea what you’re talking about.”

Jay was pissed but not really at her. Kind of at her. But mostly at himself. He was angry that his emotions had taken over, that he’d followed his heart and once again ended up in a bad spot as a result. He turned to the closed door but knew he couldn’t just leave. He had to explain even if he didn’t want to.

“You. I was just downstairs—I thought we were going to Molly’s—“

Hailey’s face clouded as she realized what he must have heard. She said his name again, this time only softly. “Jay.” She sat on the bench and looked down for a second as he still spoke.

“And what, you’re blowing me off for…for…for…” He gestured pointedly toward the door. “ _that_.. …” He was so frustrated he couldn’t get the words out. He sat on the opposite bench, and faced her.

“I forgot about Molly’s.” she conceded. “I’m sorry.” 

He took a breath. “We had plans...” He shrugged and stood, a ball of nervous energy. “Then I hear you’re going out with… _that_ _guy_?”

Hailey shrugged, and gave him a small smile. She stood as well. “Andrew's good police. You don't need me--everyone else will still be there. And...yeah. He asked me.” Her response was so genuine and so simple it made Jay freeze.

Understanding had come over her while he was speaking, and if she didn’t hate this whole thing, the position she now felt trapped in, she might have laughed thinking Jay was jealous. But she _was_ in this position and she didn’t have it in her to be anything more than tired.

Since coming back from New York, she and Jay had picked up right where they’d left off. Which was great. Except it wasn’t. It was familiar and comfortable, and she felt like she could breathe again, except it was also a giant pair of boots that were stuck in concrete and she’d stepped right into them.

While gone, she’d thought maybe the whole ‘out of sight, out of mind’ thing would come in to play, but instead it had been the ‘absence makes the heart grow fonder’ saying that she’d come to live during those weeks away. They’d talked and texted all throughout that time and she thought that when she got back there’d be some movement. From her, from him, she didn’t know, but either way there hadn’t been. And she couldn’t blame him entirely, she knew she was equally to blame. They’d gone out for deep dish, had had drinks at Molly’s, his place, her place, talked about so many different things big, small and everything in between but still never about the things she felt, the moments they seemed to get lost in, and what they meant.

Now she was _tired_. Tired of fighting her feelings for her partner, of trying to rationalize them, of not making a move, of not being honest with how she felt. And now it had been so long since she’d come to the realization that to bring it up, admit she’d been harboring these feelings for months, just seemed pathetic. She couldn’t do it and had decided to try and break free of the boots, step out of them and try to move on.

When she’d bumped in to Andrew McLaughlin, an old friend and evidence tech from forensics, down in the mailroom and he asked her out for a drink tonight, she’d said yes. It seemed like a good start. She’d known him since her days in Robbery Homicide and catching up would be a safe way take a baby step.

“Hey Sarge, you coming to Molly’s tonight?” Jay was signing out, talking to Platt as he wrote his name.

“I don’t know Halstead, you gonna be there?” She deadpanned as though his response would help decide her answer.

He smirked. “Ha-.” He put the pen down and looked at her. “-Ha.” He huffed out a light chuckle. “Hailey and I are heading over in about….15 minutes. She was just dropping something in the mail.” He gestured toward the room behind her desk.

Trudy didn’t have a chance to respond before hearing a male voice from that same area say Hailey’s name in loud surprise. Two voices exchanged quick pleasantries before hearing the same voice ask her if she wanted to catch up for drinks that night. Hers followed, saying, “Yeah. Sure. That’d be great.”

“Did… Upton know about your plans?” Trudy smart assed slowly.

Jay stood frozen at the desk only dragging his eyes to Trudy’s after she’d spoken. His brain and heart were both struggling to comprehend the fact that Hailey had just agreed to go out with some guy. Some other guy. Tonight. By the time he’d roused himself to move around the desk and to the mailroom it was empty. He went after her, compelled to find out what was going on.

And now they were in the locker room and he had heard, had found out what was going on, but he didn’t understand it. He stood there, looking at her and her looking right back. Though his face was one of confusion, some sadness, and hers was simple resignation.

Hailey picked up her jacket, tentatively putting a hand to his arm and spoke softly. “I’m sorry I forgot.” She grimaced in regret. “See you tomorrow.”

Jay couldn’t say anything as she moved past him, opened the door and disappeared down the hallway. All he could do was move a hand to his face and rub a few times before sitting down on the bench to wonder how he'd lost a night with Hailey.

Later on he sat at Molly’s with his brother, at the bar. It was late and the rest of the team had already gone home. Will had watched his brother with concern as he nursed another beer.

“Jay, we’ve been sitting here for almost an hour. If you’re not gonna tell me what’s bugging you can you at least mime it? Act it out? Write it on a napkin? Something?”

Jay glanced at Will and knew he was right. He exhaled loudly and threw a small half smirk as he took a swig from his pilsner. “If I could explain it, man, I would.” He shook his head lightly before turning in his stool and leaned back, elbows propped behind him on the back rest “You ever think things are going along ok, that they’re working out, then all of a sudden,” His eyebrows raised and his hands spread before him in the air. “--full stop?”

Will grimaced in understanding and sighed. “This is about Hailey.”

“No!” Jay’s furrowed brow and too-quick response screamed that it couldn’t be anything else, and it was obvious.

“You two still dancing around each other?” Will asked, in mild annoyance. “What’s it gonna take for one of you to make a move?”

Jay sputtered a bit. “What? No, you know it’s not like that man, we’re--

“Partners.” Will nodded as he finished both Jay’s sentence and the whiskey in his glass. He motioned to the bartender for another. “Yeah, we all get that, but Jay,” He reached forward and clasped his hand to his brother’s shoulder. “We gotta talk.”

Jay knit his brow a bit, unsure if it was the beer or his brother’s behavior that was confusing him.

Will continued. “You’ve been burned. Hard. Twice.” He held up two fingers then smiled in thanks as his new whiskey arrived. He took a sip before continuing.

Meanwhile Jay’s lips pursed thinking back to Erin, to Camila. Yeah, he’d loved Erin. And Camila? He’d been at the bottom of a dark well and thought she made things better. Loved? No. Used, he knew, was a better word. But either way, he’d burned himself with her and was by Erin when she left, never turning back.

“I mean, it’s understandable why you’d be gun-shy to take a shot again but c’mon, it’s been too long…and it’s _Hailey_.”

“What's _that_ mean?” He still felt 10 steps behind, trying to absorb what Will was saying. At a certain level he knew that he knew—but he hadn’t yet absorbed it and let the meaning in.

“Seriously.” Will said the word and looked at his brother like that one word and look should explain everything.

Jay kind of got it, was getting it, and twisted in his seat, a bit uncomfortable. Yeah, he knew he had feelings for his partner, he just never wanted to name them.

He grimaced and looked down to his beer bottle, fiddling with the cap beside it. “Will, you don’t get it, how it is—“

“Who the hell cares, Jay? You like her?” He tilted his head, craning his head to seek out his brother’s eyes. “You like her. Maybe more than that, who knows, but you doing jack about it isn’t gonna do anything. You’re gonna have to man up..” He smirked and took a drink

“' _Man up_ '?” Jay’s brow furrowed as he repeated the words.

Will’s eyebrows were up. “Man.Up.” He nodded. “Make a move, take a chance.”

Jay sighed heavily. “It’s not that easy man, she’s—“

Will interrupted immediately “If you say she’s your partner I’m leaving. Or—“ he looked at his drink. “at least--leaving you alone—I’ll go sit over there.” He motioned to some people with his glass at tables across the room.

It was quiet for a moment as Jay thought. He groaned realizing there was no easy move to make, but knew that he really did have to make one.

Will grinned in to his glass.

“Shut up.” Jay told him, then looked at him with a bit of exaggeration. “If I end up looking like an asshole, or screwing up my partnership…”

Will’s hands went up is mid-surrender. “You can punch me, right here.” He pointed to his cheek. “But I think I’m pretty safe.” He chuckled. “Think you think so too.”

In a way Jay did. His partnership, his connection to Hailey was so strong. Even if he made a fool of himself with her, she’d allow them to move past it, wouldn’t dwell on it. She’d still be his partner, all in. So really, he didn’t have anything to lose—except however long it took him to hold his breath when he waited for her response. First he had to think of what he wanted to say.

Hailey had had a nice enough time with Andrew. They went to a bar closer to area central, shared an appetizer, had had a few drinks. But that had been it. They’d caught up and now it was done. Neither had felt any kind of spark though neither was really looking for one. She’d waved good bye to his friends and walked out to her car.

The drive home was uneventful and her mind tried to keep calm, torn between not thinking of how she’d chosen to not go out with Jay tonight, to lie about forgetting their plans, and not thinking about him or them at all.

Either way, she resigned herself to the thought that the night would have been a bust no matter what. It had been with Andrew and it would have been with Jay. With both she still felt or would have felt lost and unfulfilled. She had to find a way to quell those feelings or she knew she was going to go crazy.

It was late when she twisted the key in her front door lock and opened it to the quiet. Vanessa’s car was gone so she was probably out with Kim and Kevin or maybe her academy friends. The house was cool and dark and quiet, all soothing Hailey yet making her ache more present.

She had just kicked off her shoes in the foyer when the 3 crisps knocks at her door startled her.

Opening it she was surprised to see her partner standing there.

“Jay?” she questioned.

“We need to talk.” He told her as he stood. “No.” He scrubbed his face. “ _I_ need to talk—to you.”


	2. part 2

**Summary for the Chapter:**

> Jay and Hailey talk things out. Happiness ensues. (yay!)

Hailey sighed and stepped aside, allowing Jay to enter.

He did a quick scan for anything that would say her evening out had continued back here. “You alone?”

She snorted and rolled her eyes a bit as she closed the door, following him farther in. She responded in a near groan. “Yes, Jay. No one else is here _.” Thanks for the reminder._

He stopped himself from asking if instead anyone _had_ been there but left but knew starting this conversation with pissing her off wouldn’t be his smartest move. He took off his coat and threw it on the back of the couch. “Can we sit?”

Hailey raised her eyebrows, shook her head a bit and shrugged. “Sure.” She didn’t know why he was here or what he wanted to talk about but the sooner they started the sooner they’d be done and she could go to bed.

She sat in an overstuffed chair while he sat on the couch. “What’s goin’ on?”

Jay took a breath and looked at her, twisting his mouth a bit. He was here and in it. There was no turning back. “We’ve been partners a long time.”

She nodded. “Mm hm”

“And I think, ‘friends’ for a long time in there too.”

This wasn’t any kind of topic of conversation she’d even considered they’d have tonight. Her brow furrowed a bit a bit as she settled deeper in her seat and paid better attention to Jay. Thoughts of tired and bed evaporating from her mind.

“Somewhere in there Hailey, something changed for me. Your friendship became…the best one I’ve ever had. Too important to mess with. And I didn’t want to lose it. Ever. No matter what.” He leaned forward, elbows on knees, with his hands together under his chin.

He looked to her and was relieved to see what he thought he would—Hailey’s eyes on him, no judgements, all in, listening, giving him her attention, giving him her. It gave him the courage to go on.

He swallowed once and spoke again, this time slightly slower, with a bit more hesitation. “And I hope saying... what I’m about to say doesn’t screw all that up.” He took a deep breath and rubbed his hands together as he heard Will’s stupid ‘man up’ words in his head.

“Hailey,” he stopped and quirked a smile at her. She was so perfectly ‘her’ right now—sitting in her comfortable clothes, hair pulled up, a knee drawn up to her chest, watching him intently. “somewhere between you being an amazing partner, an amazing friend…you became something else to me. Something more.”

Hailey tilted her head, not fully willing to believe she was hearing what she was. She blinked a few times and listened.

“I don’t know what to call it, how to name it. But the thought of you going out with some guy really threw me tonight. And it’s because…” He backed up a bit on the couch, happy to see she got the clue and moved herself over to sit with him. “it’s because if I had my way,” he huffed out a small facetious laugh, not believing he was actually saying any of this. “If I had my way, I’d be the only guy you spent time with.”

He looked to her, eyes on hers, head down a bit and clarified. “ _Outside_ of work.” He hoped she'd get where he was going.

Hailey did and breathed his name, not in a way that suggested pity or condescending or even shocked surprise. “ _Jay_ " A smile ghosted across her features before turning serious again.

She turned her body toward his and scooted closer. She blinked slowly a few times; he’d done such an enviable job voicing his feelings she felt compelled to do the same.

“There was a time, months ago—“ she rolled her eyes a bit and shook her head. “I wanted to have a similar conversation…when you were in the hospital.”

Jay hadn’t expected the talk to continue this way. He’d expected, hoped maybe he’d kiss her and she’d kiss him back, prayed she wouldn’t sigh and remind him of her disdain for workplace romances. He hadn’t expected her to tell him that she’d wanted this conversation too. He was so invested in this, in her, nearly drowning in hopeful expectations. And now he watched her, listening, as she had done for him.

“I hadn’t admitted it to myself until then, but these feelings, they’d been there. For a while already,” she nodded slightly, remembering. “But then there was a thought, a real possibility that you might not—“ her voice hitched and she paused. Jay reached out and with a finger, hooked under one of hers. She looked to their hands then to his face, a soft smile forming on hers. The one finger turned to all five and she was holding his hand, gaining strength and comfort from the physicality.

“I didn’t want to ruin this either Jay.” She spoke softly, looking at their hands. “I thought what we have works and I’d rather have that than nothing. I don’t know if I wasn’t ready to take the risk or was just too scared--- or thought you were…” she trailed off, worried she shouldn’t have kept going. It would have been fine to stop a few words back and she looked down, biting her bottom lip while trying to finalize her thought.

Jay hadn’t realized he’d been holding his breath while she spoke. But he did and all of a sudden let it out, exhaling slowly, deflating. He thought he might know her reasoning and he felt a shame creep up his spine.

He was somber when he spoke. “The phone call?”

Her head snapped up and her eyes met his in surprise. He remembered that? He’d known? Her head tilted slightly as she gauged what he might be talking about exactly.

“You’d been so…sincere,” he licked a lip. “Starting to talk about something you’d realized.”

Hailey realized she was holding tight to Jay’s hand and relaxed hers a bit. She was fighting the quivering of her lip as she realized she was here, in this moment.

“Yeah,” she whispered, nodding. “I…I wanted to tell you then. But the call—I thought—“

“You thought I was gonna go back to it. Get involved.”

Hearing him say it made her feel like she hadn’t believed in him, hadn’t given him a chance in that moment and as much as she never wanted to relive Jay being hurt, she found herself wishing she’d not taken the easy way out that day.

But for now, her teeth put pressure on the quiver in her lip and she nodded. “I’m so sorry.” She whispered, looking down.

He smirked self-deprecatingly and shook his head. His thumb began to stroke the skin between her thumb and finger on its own. “No, you were probably right. My head was still…” he shook his head, clearing the memory of him being so willing to see what Bobby had needed, what he could do to help. But she’d pulled him back, like she always had. And he was grateful. Again. “But now…I mean…you get what I’m saying here?”

Hailey looked up at him, eyes wide. They’d moved forward. She felt it. And she was mildly stunned by it. By them.

She nodded slowly and agreed verbally. “I do.”

He nodded as well, his eyes going to their hands, to his thumb, to the feeling of her skin prolonged under his. A small smile broke out on his face. “So….”

She huffed out a breath. “So…” she repeated.

He’d gotten this far, Jay realized. He was gonna go for broke, go for it all the way.

“Hailey,” he whispered, savoring her name on his tongue. His lips came together so he could hold this moment, where everything was possible and everything was in sync. “Somewhere along the way, knowing you and working with you and being your friend... I fell in love with you. I wish I could figure out the day…what it was….but it happened. And now…” He smiled at her, cautiously, lovingly, slowly. “I love you.”

It had been so simple to say. He was surprised that it had, but now that it was out he wanted to say it a million times, show her in a million ways. He watched her, waited for her reaction. He wanted to see the fact of his words reach her. He wasn’t disappointed.

Hailey’s breath hitched and her head tilted to the left a bit as her gaze faltered for a second. His words. She’d heard him say the words that had lived in her heart for months and now were desperate to escape and meet his.

Her smile was somewhat weak as her lips trembled as she struggled not to cry. All she could muster at first was his name and it came out more like a vibration than a word.

He chuckled. “Hey, you okay?” He reached for her and tilted her chin back up to him.

Her smile was stronger but not by much. Despite that she looked _happy_. Hailey nodded and wiped at her eyes. “I am.” she assured him. She huffed out a light laugh as she looked up at him, not sure why she was feeling so shy, so vulnerable. “I love you too.”

Another chuckle escaped Jay as he heard her say the words, heard and felt the meaning and the feeling behind each one. He squinted at her, disbelieving that they were here, that they were this good, that he had finally found this, claimed this.

She was staring at him, about to reach forward and kiss him when he moved faster. His hand snaked around her neck and pulled her forward, his eyes on hers and nothing had ever felt so right. She closed her eyes to him and parted her lips, savoring their first kiss. Soft and exploratory, new, and full of feeling. It was all either of them needed in the moment, no call to rush forward. It would all come. It would all be theirs.

He smiled happily and a tad smug as he pulled back a bit. “Just remember who said it first.”

**Notes for the Chapter:**

> Thank you to everyone who has left such kind comments and kudos! I'm always so surprised and touched when I get them! This is the last chapter of this story but I do have an afterward planned since it didn't make sense in the scope of the chapter and I didn't want to add another that would potentially just lead to another lol Hopefully that'll be up by tonight since it's mostly written.
> 
> As always, these characters aren't mine. I just get to play with them.


	3. Chapter 3

**Summary for the Chapter:**

> What happens when you've been dating for a while and things are going great? A natural step. Unless you're Jay Halstead.

Nearly a year had gone by that Jay and Hailey were dating. They’d gotten through home and work squabbles, some tough cases and a lot of fun times.

Hank wouldn’t have predicted it but their being together had truly brought out the best in each other, both on the job and, he assumed, off. The thought had been there when they announced their relationship to him and quickly scribbled through the HR forms, that he should end their partnership. Too much togetherness, personal issues getting in the way of the job, a heightened awareness of dangers, had all been reasons that he’d entertained. But in the end, he’d told them it was on them. He’d keep them partnered up until one of them requested either an out or a break, or until he saw something that could lead to a break in safety. They’d be allowed to work until they didn’t.

Jay and Hailey had nodded and accepted it. Sure, they’d swapped partners as cases needed, as people came and went for undercover, medical leaves or even personal time. There had been bad days, days where reminders had been given about keeping heads in the game, being focused on the job, days where worry had been worn on their faces as their partner worked a dangerous case, went deep undercover, or was getting too close to a particular case. But they always returned to each other strong, in sync and ready to work. 

Now, Hank stood in his office and looked through the window out into the bullpen. Hailey had just left for a must appear court date and wasn’t expected back till early afternoon. He watched the easy banter play out between the two detectives who sat closest to his office. Jay must have said something for Hailey to laugh as she did, and threw a pen across the desks at him. She shook her head lightly and rolled her eyes as she turned and walked, glancing back at him with a bright smile before she descended the stairs.

Jay continued to look straight ahead for a full minute after she’d gone before getting back to his computer.

They worked. There was no doubt about it. Hank grunted softly to himself before stepping toward the door.

“Jay. Come in here for minute?” Hank’s hands were in his front jeans pockets as he rocked a few times on his heels.

Jay had looked over to his boss and nodded. “Sure thing.”

“Close the door,” Voight gestured toward it. Then, “Take a seat.” As he sat at his own desk.

Jay sat and waited to hear whatever his boss wanted to say. An uncomfortable silence settled in the room as Hank tapped against the arm of his chair, obviously mulling something over.

“Sarge?” Jay wasn’t sure why they were sitting here in silence, much less with the door closed. A seed of worry began to grow in his stomach.

Hank grunted and sat up straighter in his seat, turning his chair so that he faced Jay directly.

“Jay, it hasn’t affected the job so outside of that it’s really not my business but….you and Hailey….”

Jay was caught by surprise and now it was his turn to sit up a bit straighter. “What about me and Hailey?”

Hank sighed, glancing at the picture frames on his desk before looking out toward the man in the chair. He grabbed a pen and began to tap it against the edge of his desk. Some emotion began to show on his face.

“My kids are gone. Justin….Erin…” A hand scrubbed at his face before he collected himself and continued. “This team, this is my family.” He nodded as he spoke. Voight opened a drawer but took nothing from it, making Jay furrow his brow a bit. “You, Hailey….all of you. With the two of you though, knowing what you’ve been through, what you’ve fought through…for---and seeing you now…Jay, I hope I’m not stepping out of line here….and I certainly hope I’m not reading down the line wrong—but should you ever want it--” More nodding from Hank as he reached in to the opened drawer and pulled out a tiny bag. He emptied the lone object from it onto the desk in front of Jay.

Jay’s eyes grew large as he saw what it was. “Hank.” He whispered, looking to him.

Voight nodded for him to take it. “I gave it to Camille one night after dinner. We’d gone out to Schaller's Pump , it’s not there anymore,” He grimaced. “But we ate and went for a walk along the river” He pointed repeatedly at the object Jay now held in his hand. “I gave her that ring that night, asked her to marry me. We had a good run, Jay. We had a good life. She was a good teacher, a great person, an amazing wife, mother—probably deserved better than me but we were good. Even through the cancer…” His voice trailed off.

Jay was touched beyond words. He didn’t know what to say as his eyes went to the piece of jewelry in his hand. The simple gold band with the small elegant diamond set on it. He’d absolutely thought of spending his life with Hailey—many, many times. But proposing was a hurdle he wasn’t ready to tackle just yet. For now, he was happy, thought they were happy with things as they were.

“Hank, thank you so much for this.” He closed a fist around the ring and pumped it a few times. “It’s beautiful, really, but I…”

“Jay, listen,” Hank put up a hand, stopping him mid-sentence. “Don’t do anything you’re not ready for. I just wanted you to know that this is here----it’s yours---for Hailey, if you ever decide you want it. And if you don’t, that’s okay too.”

Jay didn’t speak. Couldn’t have, even if he even remotely knew what to say.

Hank picked up the small bag again and offered the opening to Jay.

Jay opened his hand and looked again at what lay inside. It was beautiful and simple, and all of a sudden he could picture it on Hailey’s finger. _Someday_ he stressed to himself. Jay had trouble now, almost, parting with the ring. He realized he liked it in his hand, thinking about it, and what Hailey’s reaction would be. What it symbolized. Jay’s eyes met Hank’s and finally, near haltingly, he deposited the ring back in to it. Hank put it back inside the desk drawer and closed it.

When Jay simply continued to sit, his mind now swirling with what had just happened, the silence from the beginning of this meeting returned for a bit.

“Well, that’s it.” Hank looked at him expectantly before his eyes flicked to the door, telling Jay silently that he could leave.

“Oh yeah,” Jay startled and stood quickly. “Thanks, Sarge.”

“So he just flat out gave it to you?” Will asked in surprise, signaling for a refill on his bourbon.

Jay was finishing a drink from his pilsner and shook his head, swallowing. “Didn’t give it to me, _offered_ it to me. To give to…” He didn’t finish the words, instead shrugging a bit and looking to his brother like it should be obvious who he’d give it to. _If_ he was giving it to anyone. Which he wasn’t. Not even thinking about it.

Will chuckled, “Yeah I get how the process works.” He said off-handedly as he nodded a thanks to the bartender who delivered the fresh drink. “So you gonna do it?” Will made sure to keep his head looking straight ahead, not make eye contact with Jay as he asked that question.

Jay pulled the bottle harshly away from his mouth. “ _WhatNooo_ … what me and Hailey have is good. It’s going really well.”

“Hmm” Will murmured, smirking. He sipped and purposely avoided looking at Jay.

"Aaaand what’s that supposed to mean?” Jay rolled his eyes before accepting the new bottle of beer that appeared before him.

Will shook his head, still smirking and trying not to laugh. “Nothing, nothing!” At Jay’s look he tried to get himself together and turned toward him. “Just…if this…’direction’ is one you want to go in or even talk about, you’re gonna need to find another reason besides ‘what we have is good’ not to do it. You used that argument up before dating. That well is dry.” He huffed. “Bone fucking dry.”

Jay looked at Will and pursed his lips before taking a drink. He was annoyed to admit if only to himself that he got what his brother was saying.

Jay shrugged a bit. “It’s not worth talking about anyway. We haven’t even talked about it….” He stopped for a second. “Ever, really…” Was that right? He wondered. It had been almost a year that they’d been together, known each other for longer than that. Neither had ever really talked about the future, both happily living in the now. And that was okay. Wasn’t it?

“Uh-oh” Will pointed at him, laughing.

“What?” Jay stopped the bottle lip just below his chin and held it there.

“I made you think. What’s it about?”

The grinning was getting on Jay’s nerves. His lips twisted a bit before he rolled his eyes. “Nothin’. Just---nothin.”

“Mmm hmm” Will nodded, knowingly.

“You don’t know anything, Will. In fact,” Jay raised his beer to him. “You know shit. That’s what you know.”

“I know I still have Mom’s ring.” He deadpanned. “If you were ever gonna—“ Will’s eyes widened at Jay’s look. “What, I said IF…..” he took a breath. “If you ever wanted to go down that road, I still have it. It’s back in the security deposit box. I’m just saying…” Will shook his head with a light shrug.

Jay sipped and thought. This topic had gone from never really existing in his brain to being all he thought about, just from talking to Voight and holding that ring for all of 2 minutes. Jesus.

Thinking about that ring led him to his Mom’s. It was beautiful, he knew that first hand. But that ring had been nearly given once. He couldn’t use it again. Wouldn’t. And Voight’s had as much meaning as his mom’s did, in a way more. That ring wasn’t right for Hailey anyway. It wasn’t ‘her,’ not that he’d given any thought to what ring was ‘her’ before today. But he knew that while his mother would have loved Hailey, she’d be on board for letting that ring find a place on whomever Will chose to give it to someday. He caught himself, realizing the things he was thinking. How the hell had this happened?

“Still thinking” Will sing-songed.

“Keep it up,” Jay muttered. “Watch what happens.”

Will winked at him.

“I have no problem beating your ass right here.” He mildly, brotherly, threatened.

“Uh-OH” a new voice chirped as arms wrapped around Jay’s middle from behind. “Halstead boys fighting again?”

“Hey,” Jay smiled at Hailey’s distraction. “Nah, we’re good.” He shot Will a look, letting him know that that topic was no longer up for discussion. AT.ALL.

Will just nodded and rolled his eyes while his eyebrows raised.

“Will’s just being Will.” Jay gave one last shot, taking his aggravation with his thoughts out on the easy target. “How was court?”

Hailey took off her jacket and put it on the empty stool next to Jay. “Uhh, a nightmare. I’m gonna need a drink to even talk about it.” She signaled to the bartender and smiled at Jay, tilting her head. “You good?”

He stared at her, lost in blocking _those_ thoughts while simultaneously thinking about how much he loved her. He closed his eyes briefly as he came back to her, running a hand through her hair and pulling her in for a light kiss. “Yeah,” he told her, smiling. “All good.”

Jay swallowed hard and walked up to Voight’s office, rapping on the doorjamb a few times. He walked in as his boss’ head looked up to see him.

“Hey Jay, what's up?”

Another hard swallow. “So, ahh…I was wondering….”

Hank could see the nerves wafting off of Jay and smiled a bit. “Sidown” He gestured toward the chair.

“Yeah-yeah.” Jay said a bit too quickly even to his own ears. “I’m just gonna—“ He pivoted to close the door before going to sit. He rubbed his palms against his thighs. “Man, you should get some ac in here….it’s warm…” Jay pulled a bit at his collar, grimacing.

Voight blinked a few times, allowing himself a tiny smile before schooling his features. “Whad ya want to talk about Jay?”

Jay purposely blew out a long breath He'd been thinking this over for two weeks. Could barely think of anything else. “Okay, so…you know Hailey and I have been dating--yeah, sure you do.” He shook his head a little and tried to start over. “Um, so she’s important to me. The _most_ important, like, ever. And. I mean, I know she has parents, a _father_.” He emphasized. “But she’s not close to them, not like…” He stopped again, feeling foolish and frustrated.

Voight watched his normally cool and stoic detective basically spin out in front of him. It was something he’d never seen before, and entertaining though it was, he felt compelled to put him out of his misery.

Raising a hand to stop him, he said, “Jay, enough. I think I know where you’re goin’ with this.” His head bounced in short nods as he smiled. “I’m happy for you”

Jay expelled another long breath, grateful. His eyes were wide and he nodded. “YeahThanks,” he breathed. “And so yeah…so I wondered..” Jay’s gaze went to Voight’s desk. “If that…that ring you had….if that offer was…”

Voight nodded, smiling a bit as he reached for the drawer and opened it. When his hand reappeared it was holding the small velvet bag. He pushed it toward Jay who just stared at it.

“Just got real, huh?” Hank commented wryly.

“Uhhhhh, yeah.” He grabbed for the back of his neck and rubbed for a few seconds, before looking up in relief at his boss, smiling a little as he realized that Voight understood, knew the monumental task he was going to take on.

The little bit of lightness that had crossed Jay’s face was replaced by a more serious look almost immediately. Jay let go of his neck, and with a finger danced it around the bag a bit. “Umm, before I take that….I just wanted to make sure….” He cleared his throat. “Like I said before, Hailey’s not really close to her father…” He chanced a look up at Voight. “So” He drew out the one word. “I wondered…wanted to know….if ...so this is okay with you?”

Hank was touched and it showed. “Jay, I’m not Hailey’s father but she’s damn sure my family. You both are.” He stood and began to walk around the desk. Jay stood as he did. “If you’re asking me if you’re good to ask her to marry you, then yeah…” He took Jay in a strong hug, patting him on the back as he spoke, trying not to let the emotion be heard in his voice.

Voights affectation was affecting Jay as well.

Jay hugged him back just as hard, both of them aware that while Hailey may not have been close to her parents, Jay had neither. This was for him too.

“Jay…Ask her. Marry her. Have a _great_ life together.”

Jay stepped back, wiping at his eyes and nodding. “Thanks, Sarge.”

Hank nodded as he clasped Jay on the shoulder, gripping it. “I’m proud of you.”

Jay nearly couldn’t keep it together. He kept his head down as he reached for Hank and one more tight hug, nodding and stepping back afterward, still wiping at his eyes.

Hank nodded as he took the bag from his desk and put it in Jay’s hand.

“Thank you so much for this.” Jay rasped, closing his hand around it. He could have bought a ring but this was special. It wasn’t his mother’s ring; He’d leave that for Will. This one, this, came from a different kind of family. The kind he’d chosen.

And by giving it to Hailey, he knew he was choosing to keep that family strong and full of everything that made him happy. He was choosing to live his life with her forever.

**Notes for the Chapter:**

> Ok. There. Thinking this is it. Hope you liked it! Thank you for all of the kind comments and kudos!!
> 
> All Dick Wolf's.


	4. Epilogue--The Proposal

**Summary for the Chapter:**

> It all led to here. Jay proposes.

**Notes for the Chapter:**

> This idea was based loosely on a proposal I'd read about on ig. Everything else is mine--except the characters and whatever else is Dick Wolf's.

Hailey's feet were in Jay's lap as she lay and he sat on the couch. She'd just put her book down and looked to Jay as he was busy on his phone.

He'd had been off for a while today, not significantly but enough for her to tell. “Hey,” she lifted her chin to him. “you okay?”

He took a breath and looked away from his phone. “Uh, yeah.” His tone was light but Hailey still recognized a heaviness underneath.

She moved and sat up, snuggled up to him, and peered at his phone. “What’s so interesting on there? Someone send you naughty pictures?” She grinned at him.

He found himself laughing quietly at that, wrapping an arm around her and pulling her closer. “Those would be deleted immediately— _if_ that happened.”

She raised her eyebrows and gave him a look that might as well have said, ‘ _sure, I totally believe you’_. Instead she just smirked and went with “Mm hmmm.”

Another breath from Jay as he readjusted himself beside her. “Ummm, but I do have some pretty cool pictures on here. If you want to see…”

Suddenly there were nerves and insecurities and all things questionable racing at him, screaming not to let her look.

“Yeah?” She righted herself so that she sat more beside him than on him and pushed her hair behind her ears. “I’d love to.”

“K, hang on a sec.” Jay’s fingers weren’t working correctly, his dexterity seemingly gone as he tried to open up the album he was looking for. “It’s here, I just gotta…” He froze, landing on it. He swallowed hard and looked at her, tried to control his breathing and keep his face from flushing. If Hailey noticed any of it she didn’t say a word, just looked at him expectantly.

“Goodness, what are they of?” She laughed at his super seriousness, taking the phone from him. A thought occurred to her suddenly though and she pushed it back at him, her face blanching. “Wait these aren’t Platt and Mouch or anything…”

His brows knitted and his eyes squinted as he looked at her. “I said ‘cool pics’ not ‘gross pics.”

Hailey blew out a quiet breath and still haltingly took the phone back from him, glancing between the phone and his eyes. She had the phone in her hand again but didn’t look at it. “You sure you want me to see?” she questioned. It didn’t seem like he was that excited to share them with her.

Jay nodded solemnly and cleared his throat. “No..I do…want you to see.” But his mouth still twitched and he didn’t look too sure.

Hailey gave him a quizzical look as she settled back against the couch cushions and pulled her feet up beside her. She was still against Jay’s shoulder as well and found herself burrowing in to him as she looked at the phone screen. _Hailey_ , was the name of the album he wanted to show her.

“Me?” she looked from him to the rectangular icon. “These are of me?”

He saw her wheels turning and tried to calm and reassure her. “It’s nothing weird.” He smirked lightly. “Trust me?”

Her eyes met his and the nod she gave was barely visible. Of course she trusted him. This was just---weird.

She swallowed and braced herself for whatever these would be, thumbing the album to open it. Her brow furrowed as she saw the first picture. It was of her in the kitchen, a Sunday from a few weeks ago when she’d made pancakes. He’d caught her mid flip, unable to see the look of annoyed frustration on her face since the frame had captured her back, her head tilted and looking up to the pancake she’d flipped too high. Again. Needless to say she hadn’t caught it and their breakfast came out less in circles and more in oblong strips or broken pieces.

Her brow still wrinkled she looked to him, finding his eyes on her and his lips flattened for a second. “That’s just the first one, keep going.”

Her eyes went back to the phone and she scrolled to the next frame, this time to one of a small white box, taken just in front of where Jay had been sitting. It was a strange picture and Hailey wasn’t understanding why he’d taken these two or why he said they were cool.

The next picture answered her questions. She sucked in a breath as her eyes blew wide open. This was the same thing as the first one but now Jay was holding something out as her back was still turned.

A ring.

Hailey felt the chill rush through her as her skin responded with goosebumps. She looked to Jay again, her eyes wide and filled with love and questioning.

“Keep going.” He whispered.

She paused, her eyes still on him for a few extra seconds before dragging them back to the phone. The next picture was of her at her desk, working on the computer, the ring again outstretched before him as he took the picture. The others were the same and she had never noticed. Hailey walking ahead of him and down the stairs of the bullpen, zipping up her coat before they went outside, head down, blonde hair around her face as the black beanie hat kept the top in place. She was listening to Voight in the next one, her arms crossed in front of her as she leaned against a desk. Voight’s eye was directly on Jay as he took the picture. He must have known. There were a few more, Hailey at Molly’s, Hailey reading, Hailey eating popcorn and watching a movie, all with the ring in the foreground of the frame and her none the wiser.

In the last she was sleeping. Soundly she guessed because she had no memory of this. Her head was on her pillow and her arm bent with her palm facing upward by her head. In the middle of her palm was the ring. She’d smiled at them all, but this one made her breath hitch and her smile falter. It was so much.

She scrolled to the next picture but it was of nothing. Just a black empty frame.

“Jay?” she whispered. Even this low, her voice was filled with emotion.

She watched his adam’s apple bob as he swallowed and lift up a bit to reach for something in his front pocket. Hailey’s heart ramped up to the next level and she wondered if he could hear it beating, so fast, so loud.

Her eyes stayed on what was now in his hand, the same white box as the second picture. She looked up to him as he withdrew the arm from around her and turned his body fully toward her. She mirrored the action so that she faced him as well.

“That last one, that’s where I was hoping this would go.” Jay had the box facing him and opened it slowly before turning it toward Hailey.

He spoke quietly but surprisingly surely. “Hailey, you’re everything to me. I love you.” His lips came together for a second. “You not being a part of my life, I don’t even remember what that’s like. And I don’t ever want to know. I want to spend my life with you Hailey. Every day. And just…love you, and be with you.” He stopped and touched his tongue to his lip. “This, actually, this ring belonged to someone. To Camille Voight.” Hailey’s eyes flew up from the ring to Jay. “He offered to you, to us, hoping that we would have as happy of a life as they did. --Hailey,” He was so nervous but couldn’t help the smile that was creeping across his face. He was really saying it, doing it. “Would you….will you…marry me?”

Hailey’s lower lip rolled inward as her teeth came down on it lightly. She looked at the ring Jay was holding out to her, thought about the life he was offering. She swallowed and looked up to him, a shy smile forming as she did so.

In all of her life Hailey had always wanted--- wanted to be loved, wanted to be respected, wanted to be important to some _one_ , be important to somet _hing_. She also wanted _not_ to want, because she knew the hurt would be unbearable if she ever got those things and lost them, if she came close and let them slip away.

Jay had given her all of the firsts and erased the last. At the beginning, after realizing her feelings for him, she’d taken a tentative step toward telling him. But she’d been too scared to want, too scared to get, and took 50 steps backward. Slowly, she’d walked back, took the chance on wanting, getting, and had gotten. So much.

She’d gotten love, support, respect, intimacy, trust, laughter, friendship, and more. She’d gotten to give her heart, and gotten Jay’s in return. She’d gotten happiness.

So looking now at what he was offering, what he was asking, there was no decision to be made. There was only ever one direction to move in.

His eyes were on her and his face showed nothing but love and sheer vulnerability.

“Marry me Hailey.” His voice was raspy, breaking with restrained emotion.

“I. **_love_** _._ you” she whispered, her lower lip quivering. She desperately wanted him know how much, how he lived in her heart. She leaned forward and kissed him—softly but with all of the emotion and love that she had.

When she pulled back she took the hand that offered the ring in both of hers and held them both protectively.

“Yes” she whispered, nodding.

“Yes?” Jay wasn’t sure he’d heard her correctly. He’d been listening so hard he worried he hadn’t actually heard anything.

The smile that grew across her face, brightening it and putting every dimple on display, would have been enough for him to know her answer but she followed it up with repeating her answer.

Nodding, smiling, loving, she repeated, “Yes. Yeah. Yeah Jay—I’ll marry you.”

His lips were sealed so the force of air that rushed up from his chest came out in a light huff through his nose. His mouth formed a disbelieving smile as the fear and hope was replaced by pure joy and love. _She said_ _yes_.

He moved then, sliding the ring down her finger, and looked to her again. “You said you’d marry me.” His voice was low and quiet, filled with awe. “We’re gonna get married.” He told her as if saying it would cement it, make it real.

Hailey was nodding, grinning, teary with joy, as he grinned right back at her.

He wanted to kiss her, seal the moment. But first… “Hang on a sec,” he took the phone back and opened the camera. He took a picture first of just her finger, now with the ring in its rightful place upon it. Then one of her, absolutely glowing with love, and added them to the album, replacing the black with these two new ones, the ones that symbolized their love and the promise of their future. Together.

Then he leaned forward, placing a hand behind her neck and the other around her back as he lowered her the short distance to the floor. The quick move took her by surprise.

“Jay!” she laughed into his mouth as he kissed her, his body above hers, pressing tightly against her.

He pulled back just for a second, pausing above her just to see her one more time, in the moment she agreed to be his forever.


End file.
